Hydrophobic surfaces in oligosaccharides: linear dextrims are amphiphilic chains

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Abstract

Polysaccharide chains are usually considered to be highly hydrophilic since they have no obvious nonpolar moieties in them. Yet, it is possible to realise conformations in these chains wherein all the hydroxy groups are disposed in one side or face of the chain and the hydrogens disposed in the other. We experimentally demonstrate that such an amphiphilic surface is present in linear oligomeric dextrins, i.e., α-1,4-linked d-glucosides, but not in α-1,6-d-glucosides (dextrans) or in β-1,4-d-glucosides (cellulose). This amphiphilicity is generated as a consequence of the stereochemical constraints, which vary with the structure of the sugar and with the type of linkage. Oligosaccharide chains that can adopt incipient helical structures might display amphiphilicity. This property might be relevant to intermolecular recognition on cell surfaces, lectin-sugar binding, antigen-antibody interactions and the like, and might be manifested more in hetero-molecular recognition processes than as homomolecular self-aggregation.

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